Frank Sinatra Red Pocket Square: An Iconic Style Detail

Frank Sinatra remains an enduring icon, not just for his legendary voice but also for his impeccable, influential style. His suave demeanor and sharp dressing defined an era of cool sophistication. While many recall his signature fedoras and perfectly tailored suits, certain smaller details became synonymous with the Chairman of the Board’s look. One such element, often discussed by style aficionados, is the Frank Sinatra Red Pocket Square. Although his on-screen attire sometimes adhered to character or convention, his personal style often featured bolder choices, particularly when it came to this classic accessory, famously favoring orange, a color closely related to red in its visual impact. Examining his look in the 1956 film High Society provides a fascinating contrast between cinematic styling and Sinatra’s real-life sartorial preferences.

The Tuxedo in High Society: Classic But Missing a Signature Touch

In High Society, the glittering musical remake of The Philadelphia Story co-starring Bing Crosby and Grace Kelly, Sinatra played Macauley “Mike” Connor, a tabloid reporter assigned to cover a high-society wedding in Newport. For an evening reception scene, Sinatra dons a midnight blue dinner suit, embodying the formalwear trends of the mid-1950s.

Frank Sinatra looking sharp in his midnight blue tuxedo as Mike Connor in the 1956 film High Society.

The single-breasted dinner jacket showcased the era’s preferred silhouette: a full cut with soft, wide shoulders, drape through the chest, and a suppressed waist. Tailored by Helen Rose, the costume designer, the jacket flattered Sinatra’s lean frame while adhering to contemporary fashion. As noted by Black Tie Guide, this look—lighter worsted wool, single-breasted jacket, shawl collar, turndown collar shirt, and narrow bow tie—was quintessential fifties formalwear.

Close-up of Frank Sinatra's single-breasted midnight blue dinner jacket with self-faced shawl lapels in High Society.

However, certain details hinted at the slightly relaxed formality creeping into American menswear. The jacket featured self-faced shawl lapels rather than traditional silk or satin facings. The single front button and three cuff buttons appeared to be standard plastic, not fabric-covered. It included jetted hip pockets and a welted breast pocket. Crucially, in this breast pocket, Mike Connor wears a neatly folded white pocket square. The jacket was ventless, maintaining a clean line.

Rear view showcasing the ventless back of Frank Sinatra's tuxedo jacket in High Society, highlighting the 1950s cut.

The matching midnight blue formal trousers were made from the same lightweight worsted material. They featured pleats, a wide satin stripe down each leg (with side pockets cut behind the stripe), and a full cut tapering slightly to plain-hemmed bottoms.

Detail of Frank Sinatra's midnight blue formal trousers featuring the satin side stripe, part of his High Society tuxedo.

Sinatra’s character paired the suit with a white formal shirt featuring a pleated front, mother-of-pearl buttons, a large turndown point collar, and double (French) cuffs fastened with gold rectangular links. A slim, black satin batwing-style bowtie and a matching black satin cummerbund completed the neckwear and waist covering, adhering to black-tie norms despite the jacket’s less formal lapels. For footwear, Mike wore polished black patent leather cap-toe balmorals with black dress socks – the correct choice for formal evening attire. A gold tank-style watch on a black leather strap was visible on his wrist.

Frank Sinatra pouring champagne in High Society, showing his formal shirt's double cuffs and gold rectangle cufflinks.

While impeccably turned out for the film’s setting, the tuxedo’s white pocket square contrasts with what became known as Sinatra’s personal preference.

The Real Sinatra: Why Orange (and Red) Was His Go-To Color

Off-screen, Frank Sinatra cultivated a distinct personal style, often injecting personality through accessories. While the white pocket square seen in High Society was standard, Sinatra himself had different ideas, particularly regarding color. Bill Zehme, in his insightful book The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’, documented Sinatra’s personal style rules and preferences. When discussing black tie, Sinatra stated:

Pocket handkerchiefs are optional, but I always wear one, usually orange, since orange is my favorite color.

This preference for orange, a vibrant and confident hue, became a subtle trademark. While the specific mention is orange, the association often extends to the similar boldness of a Frank Sinatra Red Pocket Square in style discussions. Wearing a brightly colored pocket square, especially orange or red, against the dark backdrop of a tuxedo or suit jacket, was a way Sinatra added individual flair to conventional attire. It reflected his larger-than-life personality – bold, confident, and unwilling to completely fade into the background, even in formalwear. Orange, his stated favorite, likely appealed to his passionate nature and perhaps his Italian heritage, where vibrant colors often feature prominently. A red pocket square carries a similar energy, signifying power, passion, and presence – all qualities associated with Sinatra.

Iconic photo of Frank Sinatra sharing Jack Daniel's whiskey with Dean Martin and Sammy Davis Jr., embodying Rat Pack camaraderie.

This choice distinguished him from more conservative dressers of the era. While black tie traditionally called for a white linen or silk handkerchief, Sinatra’s splash of color was a deliberate style statement, much like his perfectly tilted hat or the ever-present cigarette or glass of Jack Daniel’s. It was part of the carefully constructed, yet seemingly effortless, persona of cool that defined him.

Incorporating the Frank Sinatra Red Pocket Square Flair Today

The enduring appeal of Sinatra’s style lies in its blend of classic tailoring and personal touches. The Frank Sinatra red pocket square (or his favored orange) exemplifies how a small accessory can significantly impact an outfit and convey personality. While the High Society tuxedo represents textbook 1950s elegance, incorporating a vibrant pocket square, as Sinatra did in real life, elevates the look from merely correct to distinctively stylish.

For those looking to channel Sinatra’s confidence in their formalwear today:

• Choose Bold Color: Don’t shy away from a red or bright orange silk pocket square with a tuxedo or dark suit. It adds a focal point and energy.
• Keep it Simple: Sinatra often preferred a simple puff or square fold for his colored pocket squares, letting the color speak for itself rather than an elaborate fold.
• Context Matters: While Sinatra broke the ‘white only’ rule, consider the event’s formality. A brightly colored square works best at celebratory events rather than the most solemn or conservative occasions.
• Confidence is Key: Ultimately, wearing a bold accessory like a red pocket square is about attitude. Wear it with the same self-assuredness Sinatra projected.

Frank Sinatra singing with drink in hand, offering a glimpse of his gold tank watch in High Society.

The contrast between the white pocket square in High Society and Sinatra’s real-life preference highlights the difference between costume design adhering to norms and personal style expressing individuality.

Beyond the Pocket Square: Sinatra’s Enduring Style Legacy

Sinatra’s influence on men’s style extends far beyond the pocket square. His mastery of tailoring, his iconic fedoras, his effortless way of wearing a suit or tuxedo – it all contributed to his status as a fashion icon. He understood the power of presentation and used clothing to enhance his charismatic persona. Key elements included:

• Impeccable Fit: Sinatra’s clothes were always perfectly tailored, enhancing his silhouette.
• Quality Materials: He favored high-quality fabrics that draped well.
• Signature Accessories: Beyond pocket squares, his hats and simple, elegant cufflinks were key parts of his look.
• Attitude: Perhaps most importantly, he wore his clothes with unparalleled confidence and swagger.

His dedication to looking sharp was legendary. Zehme’s book recounts Sinatra’s advice on maintaining a tuxedo’s appearance: “Try not to sit down because it wrinkles the pants. If you have to sit, don’t cross your legs.” This meticulous attention to detail underscored his belief that dressing well was a way of life.

Frank Sinatra's iconic tuxedo look from High Society, often associated with his classic style.

Conclusion

While Frank Sinatra presented a picture of classic 1950s formalwear with a white pocket square in High Society, his personal style often favored a bolder statement. The Frank Sinatra red pocket square, or more accurately his preferred orange, stands as a testament to his individuality and confidence. This small but significant detail captures the essence of his approach to style: rooted in classic elegance but always infused with personal flair and a touch of swagger. It’s a reminder that true style isn’t just about following rules, but about knowing how and when to break them with purpose and personality, solidifying Sinatra’s place as an enduring icon of men’s fashion.

References

• Zehme, Bill. The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’. HarperCollins, 1997.